Water → 2-((4-Acetamidophenoxy)carbonylamino)ethanesulfinic acid

HRID 571162Notes

Reaction equation

HRID 571162 reaction equation
[C:1](=[O:23])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[NH2:24][CH2:25][CH2:26][S:27]([O-:29])=[O:28].[Na+].OC1C=CC(NC(=O)C)=CC=1.O>C(#N)C>[C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][C:1]([NH:24][CH2:25][CH2:26][S:27]([OH:29])=[O:28])=[O:23])=[CH:8][CH:7]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 20589122Sodium 2-aminoethanesulfinateHCID 594879154-Acetamidophenyl 4-nitrophenyl carbonate2×

Product 1

HCID 715356462-((4-Acetamidophenoxy)carbonylamino)ethanesulfinic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Title compound 11a was prepared according to the General Method for the Reaction of Alkali Metal Salts of Amino Acid Derivatives with 4-Acetamidophenyl 4-Nitrophenyl Carbonate (3). A solution of 410 mg (3.20 mmol) of sodium 2-aminoethanesulfinate (5) in approximately one (1) mL of degassed water was reacted with a solution of 4-acetamidophenyl 4-nitrophenyl carbonate (3) (1.01 g, 3.19 mmol) in 10 mL of acetonitrile (MeCN). After work-up procedures, the aqueous layer was lyophilized off to afford 910 mg (˜quantitative yield) of the crude 2-((4-acetamidophenoxy)carbonylamino)ethanesulfinic acid (11a) which was used directly and without further isolation or purification procedures in the next step. The material thus obtained was contaminated with some sodium chloride (NaCl) and/or other sodium salts. 1H NMR (300 MHz, D2O): δ 7.22 (d, J=9.0 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 3.31 (t, J=6.6 Hz, 2H), 2.42 (t, J=6.6 Hz, 2H), 1.96 (s, 3H). LC/MS (ESI): m/z=287.1 [M+H]+.

Workup

  1. customTitle compound 11a was prepared

Sources & evidence

ORD record
ord-1f70fd52382d41cd9f430b704b953ed7
Source dataset
uspto-grants-2015_05
Patent number
US09024055B2

Reaction notes

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